methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106507
• Molecular Formular: C31H39FN4O9
• Molecular Mass: 630.6611632
• Monoisotopic Mass: 630.27010707
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)OCc1ccccc1)C(C)C)C(=O)CF
• Canonical SMILES: COC(=O)C[C@@H](C(=O)CF)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C31H39FN4O9/c1-18(2)27(30(42)33-19(3)28(40)34-23(25(38)16-32)15-26(39)44-4)36-29(41)24(14-20-10-12-22(37)13-11-20)35-31(43)45-17-21-8-6-5-7-9-21/h5-13,18-19,23-24,27,37H,14-17H2,1-4H3,(H,33,42)(H,34,40)(H,35,43)(H,36,41)/t19-,23-,24-,27-/m0/s1
• InChIKey: MVPQJUFFTWWKBT-LBDWYMBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Tyr-Val-Ala-Asp(OMe)-FMK; Z-YVAD(OMe)-FMK; Z-Tyr-Val-Ala-Asp(OMe)-Fluoromethylketone

Database IDs

• PubChem SID: 162105503
• PubChem CID: 644196

CALCULATED PROPERTIES

• Acid pKa: 9.499466
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 2.122107
• LogD (pH = 7.4): 2.1187336
• Log P: 2.1221502
• Molar Refractivity: 158.0307 cm^3
• Polarizability: 61.757175 Å^3
• Polar Surface Area: 189.23 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK013

A potent, cell-permeable, and irreversible inhibitor of caspase-1 (ICE), caspase-4, and caspase-5.

REFERENCES

• Thornberry, N. et al., Persp. in Drug Disc. and Design, 2:389 (1994).
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Eldadah, B.A., et al. 1997. J. Neurosci. 17, 6105.